Nitrile derivatives as perfuming ingredients

ABSTRACT

The present invention concerns substituted benzylic nitrites substituted with lower linear alkyl or alkylene groups. These compounds are useful perfuming ingredients, and can impart odor notes of the floral-green type. The invention concerns also the perfuming compositions or perfumed articles associated with the compound.

TECHNICAL FIELD

The present invention relates to the field of perfumery. Moreparticularly, it concerns substituted benzylic nitrites which are usefulas perfuming ingredients, in particular to impart odor notes of thefloral-green type.

BACKGROUND

Amongst the compounds of formula (I), as defined below, a few are known.In particular, all the compounds wherein the dotted line represents adouble bond have been previously described for various purposes such aschemical intermediates (for example: α-butylidene-benzeneacetonitrilehas been reported by S. I. Murahashi et al. in Synlett, 2000, 1016).However, none of the prior art documents disclosing a compound offormula (I) reports or suggests any organoleptic properties of theinvention's compounds, or any use of these compounds in the field ofperfumery.

The compounds described in EP application 682010 or in U.S. Pat. No.6,069,125 are the known perfuming ingredients having the closeststructure to the invention's compounds. However, the invention'scompounds not only differ from the prior art compounds in their chemicalstructure but also in the organoleptic properties which are, in the caseof the prior art, of the of the marine or rosy-fruity (sweet) type.Nowhere in these two patents there is a suggestion of any usefulness ofthe invention's compounds in the field of perfumery, and even less ofany organoleptic properties of the present compounds.

SUMMARY OF THE INVENTION

The present invention now relates to the use as perfuming ingredients ofa particular benzylic nitrile as well as to the perfuming compositionsor the perfumes articles containing the invention's nitrile. Furthermorethe invention relates also to a new method for the preparation ofbenzylic nitrites.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

We have now surprisingly discovered that a compound of formula

-   -   wherein R¹ is a C₁₋₄ linear alkyl group, and    -   a) the dotted line represents a double bond having a        configuration E or Z or a mixture thereof, and R² is a hydrogen        atom; or    -   b) the dotted line represents a single bond, and R² is a C₁₋₄        linear alkyl group;        can be used as perfuming ingredient, for instance to impart odor        notes of the floral type.

According to a particular embodiment of the invention, R¹ represents aC₂-C₃ linear alkyl group, and in particular a n-propyl group.

According to any of the above mentioned embodiments, the compoundswherein the dotted line represents a double bond are preferred, and inparticular those having this double bond in a configuration essentiallyZ, i.e. the Z isomer representing at least 90% relative to the weight ofthe mixture.

Amongst the compounds of formula (I) those wherein the dotted linerepresents a single bond and

-   i) R¹ is a C₃₋₄ linear alkyl group and R² is a methyl group; or-   ii) R¹ is a C₁₋₄ linear alkyl group and R² is a C₂₋₄ linear alkyl    group    are new and are an object of the present invention.

Amongst the compounds of formula (I), one may cite in particular, and asnon-limiting example, (2Z)-2-phenyl-2-hexenenitrile. This compound has asubstantive and powerful floral, green-floral, odor with jasmine-muguet,lilac, herbal-lavender-rosemary notes. The overall odor of this compoundhas a strong hexylcinnamic aldehyde connotation (i.e. herbaceous-floral)and is also slightly green-geranium (e.g. of the diphenyl oxide type).The odor of the invention's compound has also bottom notes presentingamyl salicilate and chocolate aspects.

More interesting, this compound can also display citrus or citronellanotes depending on the medium into which it is incorporated, as will befurther illustrated in the examples.

When compared to the prior art compound 2-phenyl-2-hexanenitrile (see EPapplication 682010) the invention's compound distinguishes by lacking,or by not possessing significant, anethole/carvone-like undernotes, aswell as by lacking, or by not possessing significant, fruity (pineapple)and rosy note notes which are characteristic of the prior art compound.This difference lends to (2Z)-2-phenyl-2-hexenenitrile and2-phenyl-2-hexanenitrile to be each suitable for different uses, i.e. toimpart different organolpetic impressions.

Another example of invention's compound is2-(4-methylphenyl)hexanenitrile which possesses an odor withfloral-jasmine and geranium notes as well as nitrilic and fruity notes.The overall scent is close to the fragrance of hexylcinnamic aldehyde.

Yet another example of invention's compound is2-(4-ethylphenyl)pentanenitrile which is characterized by a niceflorale-jasminic and hyacinth note having also a coumarine aspect. Thebottom notes of this compound reminds of the odor of hexylcinnamicaldehyde.

These last two compounds named do not have or are almost devoid of aparticular fruity or rosy connotation, to the contrary of2-phenyl-2-hexanenitrile (see EP application 682010)

Amongst the compounds of formula (I), (2Z)-2-phenyl-2-hexenenitrile and2-(4-methylphenyl)hexanenitrile are the preferred ones.

As mentioned above, the invention concerns the use of a compound offormula (I) as perfuming ingredients. In other words it concerns amethod to confer, enhance, improve or modify the odor properties of aperfuming composition or of a perfumed article, which method comprisesadding to the composition or article an effective amount of at least acompound of formula (I). By “use of a compound of formula (I)” it has tobe understood here also the use of any composition containing compound(I) and which can be advantageously employed in perfumery industry asactive ingredients.

These compositions, which are in fact perfuming compositions that can beadvantageously employed as perfuming ingredients, are also an object ofthe present invention.

Therefore, another object of the present invention is a perfumingcomposition comprising:

-   i) as a perfuming ingredient, at least one inventive compound as    defined above;-   ii) at least one ingredient selected from the group consisting of a    perfumery carrier and a perfumery base; and-   iii) optionally at least one perfumery adjuvant.

By “perfumery carrier” we mean here a material which is practicallyneutral from a perfumery point of view, i.e. that does not significantlyalter the organoleptic properties of perfuming ingredients. This carriermay be a liquid or a solid.

As liquid carrier one may cite, as non-limiting examples, an emulsifyingsystem, i.e. a solvent and a surfactant system, or a solvent commonlyused in perfumery. A detailed description of the nature and type ofsolvents commonly used in perfumery cannot be exhaustive. However, onecan cite as non-limiting examples solvents such as dipropyleneglycol,diethyl phthalate, isopropyl myristate, benzyl benzoate,2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, which are the mostcommonly used.

As solid carrier one may cite, as non-limiting examples, absorbing gumsor polymers, or yet encapsulating materials. Examples of such materials,for example, may comprise wall-forming and plasticizing materials, suchas mono, di- or trisaccharides, natural or modified starches,hydrocolloids, cellulose derivatives, polyvinyl acetates,polyvinylalcohols, proteins or pectins, or yet the materials cited inreference texts such as H. Scherz, Hydrokolloids: Stabilisatoren,Dickungs- und Gehermittel in Lebensmittel, Band 2 der SchriftenreiheLebensmittelchemie, Lebensmittelqualitat, Behr's VerlagGmbH & Co.,Hamburg, 1996. The encapsulation is a well known process to a personskilled in the art, and may be performed, for instance, using techniquessuch as spray-drying, agglomeration or yet extrusion; or consists of acoating encapsulation, including coacervation and complex coacervationtechniques.

Generally speaking, by “perfumery base” we mean here a compositioncomprising at least one perfuming co-ingredient.

This perfuming co-ingredient is not of the formula (I). Moreover, by“perfuming co-ingredient” it is meant here a compound, which is used inperfuming preparation or composition to impart a hedonic effect. Inother words such a co-ingredient, to be considered as being a perfumingone, must be recognized by a person skilled in the art as being able toimpart or modify in a positive or pleasant way the odor of acomposition, and not just as having an odor.

The nature and type of the perfuming co-ingredients present in the basedo not warrant a more detailed description here, which in any case wouldnot be exhaustive, the skilled person being able to select them on thebasis of its general knowledge and according to intended use orapplication and the desired organoleptic effect. In general terms, theseperfuming co-ingredients belong to chemical classes as varied asalcohols, aldehydes, ketones, esters, ethers, acetates, nitrites,terpene hydrocarbons, nitrogenous or sulphurous heterocyclic compoundsand essential oils, and the perfuming co-ingredients can be of naturalor synthetic origin. Many of these co-ingredients are in any case listedin reference texts such as the book by S. Arctander, Perfume and FlavorChemicals, 1969, Montclair, N.J., USA, or its more recent versions, orin other works of a similar nature, as well as in the abundant patentliterature in the field of perfumery. It is also understood that theseco-ingredients may also be compounds known to release in a controlledmanner various types of perfuming compounds.

Generally speaking, by “perfumery adjuvant” we mean here an ingredientcapable of imparting additional added benefit such as a color, aparticular light resistance, chemical stability, etc. A detaileddescription of the nature and type of adjuvant commonly used inperfuming bases cannot be exhaustive, but it has to be mentioned thatthese ingredients are well known to a person skilled in the art.

An invention's composition consisting of at least one compound offormula (I) and at least one perfumery carrier represents a particularembodiment of the invention as well as a perfuming compositioncomprising at least one compound of formula (I), at least one perfumerycarrier, at least one perfumery base, and optionally at least oneperfumery adjuvant.

It is useful to mention here that the possibility to have, in thecompositions mentioned above, more than one compound of formula (I) isimportant as it enables the perfumer to prepare accords, perfumes,possessing the odor tonality of various compounds of the invention,creating thus new tools for their work.

Its is also understood here that, unless otherwise indicated ordescribed, any mixture resulting directly from a chemical synthesis,e.g. without an adequate purification, in which the compound of theinvention would be involved as a starting, intermediate or end-productcould not be considered as a perfuming composition according to theinvention.

Furthermore, the invention's compound can also be advantageously used inall the fields of modern perfumery to positively impart or modify theodor of a consumer product into which the compound (I) is added.Consequently, a perfumed article comprising:

-   i) as perfuming ingredient, at least one compound of formula (I) as    defined above; and-   ii) a consumer product base,    is also an object of the present invention.

For the sake of clarity, it has to be mentioned that, by “consumerproduct base” we mean here a consumer product which is compatible withperfuming ingredients. In other words, a perfumed article according tothe invention comprises the functional formulation, as well asoptionally additional benefit agents, corresponding to a consumerproduct, e.g. a detergent or an air freshener, and an olfactiveeffective amount of at least one invention's compound.

The nature and type of the constituents of the consumer product do notwarrant a more detailed description here, which in any case would not beexhaustive, the skilled person being able to select them on the basis ofits general knowledge and according to the nature and the desired effectof the product.

Examples of suitable consumer products include solid or liquiddetergents and fabric softeners as well as all the other articles commonin perfumery, namely perfumes, colognes or after-shave lotions, perfumedsoaps, shower or bath salts, mousses, oils or gels, hygiene products orhair care products such as shampoos, body-care products, deodorants orantiperspirants, air fresheners and also cosmetic preparations. Asdetergents there are intended applications such as detergentcompositions or cleaning products for washing up or for cleaning varioussurfaces, e.g. intended for textile, dish or hard-surface treatment,whether they are intended for domestic or industrial use. Other perfumedarticles are fabric refreshers, ironing waters, papers, wipes orbleaches.

It has to be mentioned that the invention's compounds, due to theirchemical structure, which renders them quite resistant to manyaggressive medium, are particularly suitable for the preparation ofperfuming composition for the functional perfumery.

The proportions in which the compounds according to the invention can beincorporated into the various aforementioned articles or compositionsvary within a wide range of values. These values are dependent on thenature of the article to be perfumed and on the desired organolepticeffect as well as the nature of the co-ingredients in a given base whenthe compounds according to the invention are mixed with perfumingco-ingredients, solvents or additives commonly used in the art.

For example, in the case of perfuming compositions, typicalconcentrations are in the order of 0.001% to 15% by weight, or evenmore, of the compounds of the invention based on the weight of thecomposition into which they are incorporated. Concentrations lower thanthese, such as in the order of 0.01% to 10% by weight, can be used whenthese compounds are incorporated into perfumed articles.

The compounds of formula (I) can be synthesized by a new and originalprocess, which is also an object of the present invention.

The inventive process is particularly useful for the preparation of acompound of formula

wherein R³ and R⁴ represent, independently from each other, a hydrogenatom or a C₁₋₄ linear alkyl or alkoxy group, and R⁵ represents a C₁₋₈linear or branched alkyl;by reacting a nitrile of formula

wherein R³ and R⁴ have the meaning indicated above;with an alcohol of formula R⁵′CH₂OH, wherein R⁵′ represents a C₁₋₈linear or branched alkyl or alk-2-enyl;in the presence of a catalytic system, the process being characterizedin that the reaction temperature is above 100° C. and the catalyticsystem is a mixture comprising a base, having a pK_(a) above 13, and acomplex selected from the group consisting of [RuCl₂(p-cym)]₂ and[RuCl₂(p-cym)(PPh₃)], p-cym meaning p-cymene.

When R⁵, in formula R⁵CH₂OH, represents an alkyl group then there isobtained a compound of formula (II) wherein the dotted line represents asingle bond. When R⁵, in formula R⁵CH₂OH, represents an alk-2-enyl groupthen there is obtained a compound of formula (II) wherein the dottedline represents a double bond.

The complex is generally used in an amount ranging from 0.001 to 0.01molar equivalent relative to the amount of compound of formula (III).

Typical examples of base useful for the invention's process are KOH,NaOH or DBU. Moreover, preferably, the base is present in an amount ofabout 5 to 15 molar equivalents relative to the amount of the complex.

Furthermore, in the process the alcohol R⁵CH₂OH may advantageously beused as solvent, i.e. in a large excess compared to the amount ofcompound of formula (III).

Preferably, the compounds of formula (II) are those of formula (I).

EXAMPLES

The following examples are further illustrative of the presentinvention's embodiments, and further demonstrate the advantages of theinvention relative to the prior art teachings. In the followingexamples, the abbreviations have the usual meaning in the art, thetemperatures are indicated in degrees centigrade (° C.); the NMRspectral data were recorded in CDCl₃ (if not stated otherwise) with a400 or 100 MHz machine for ¹H or respectively ¹³C, the chemicaldisplacements δ are indicated in ppm with respect to TMS as standard,the coupling constants J are expressed in Hz.

Example 1

Synthesis of Compounds of Formula (I) According the Invention's Process

-   a) Preparation of (2Z)-2-phenyl-2-hexenenitrile

A 500 ml three necked flask equipped with a magnetic stirring bar and anargon inlet-outlet, was charged with benzylnitrile (17.6 g, 150 mmol),crotyl alcohol (86.54 g, 1.2 mol, trans/cis mixture: 23/1), potassiumhydroxide (420.9 mg, 7.5 mmol) and [RuCl₂(p-cym)]₂ (229.8 mg, 0.38mmol). The flask was then evacuated, back filled with argon and heatedat 100° C. for 1.5 hour. When the reaction was terminated, the reactionmixture was cooled and poured into water (500 ml), extracted with AcOEt(3×100 ml). The organic phases were dried over anhydrous MgSO₄, filteredand the solvent was removed in vacuo. Distillation under reducedpressure gave the desired nitrile with a yield of 45%.

¹H-NMR analysis of this mixture showed also that nitrile was present asa mixture of two diastereomers (Z/E=95/5).

B.p.: 121-123° C. /5.4 mbar ¹³C NMR: 146.9 (d), 133.3 (s), 128.9 (d),128.8 (d), 125.6 (d), 116.7 (s, CN), 116.1 (s), 34.1 (t), 22.0 (t), 13.7(q).

¹H NMR: 7.54-7.50 (m, 2H), 7.40-7.30 (m, 3H), 6.82 (t, J=7.7, 1H), 2.56(dt, J=7.7, 7.2, 2H), 1.59 (sext, J=7.2, 2H), 1.01 (t, J=7.2, 3H).

-   b) Preparation of 2-(4-methylphenyl)hexanenitrile

A 500 ml three necked flask equipped with a magnetic stirring bar and anargon inlet-outlet, was charged with 4-methylbenzylcyanide (19.73 g, 150mmol), 1-propanol (89.1 g, 1.2 mol), potassium hydroxide (423.5 mg, 7.5mmol) and [RuCl₂(p-cym)]₂ (232.6 mg, 0.375 mmol). The flask was thenevacuated, back filled with argon and heated at 100° C. for 1 hour. Whenthe reaction was terminated, the reaction mixture was cooled to roomtemperature and concentrated in vacuo. The residue was taken into Et₂O(500 ml) and washed with water (3×50 ml). The organic phase was driedover anhydrous MgSO₄, filtered and the solvent was removed in vacuo.Distillation under reduced pressure gave the desired nitrile with ayield of 70%.

B.p.: 105-106° C. /1.3 mbar.

¹³C NMR: 137.7 (s), 133.1 (s), 129.7 (d), 127.1 (d), 121.1 (s, CN), 36.9(d), 35.6 (t), 29.1 (t), 22.1 (t), 21.0 (q), 13.8 (q).

¹H NMR: 7.19 (AB syst. J_(AB)=8.2, 4H), 3.72 (dd, J=8.4, 6.4, 1H), 2.34(s, 3H), 1.95-1.78 (m, 2H), 1.52-1.29 (m, 4H), 0.89 (t, J=7.2, 3H).

-   c) Preparation of 2-(4-ethylphenyl)pentanenitrile

Following the same procedure given in b), 4-ethylbenzylcyanide (5.08 g,35 mmol), 1-propanol (21 ml, 280 mmol) were reacted with potassiumhydroxide (99.1 mg, 1.75 mmol) and [RuCl₂(p-cym)]₂ (55.1 mg, 0.09 mmol)at 100° C. for 1 h. Removal of the solvent and distillation underreduced pressure gave the desired nitrile with a yield of 51%.

B.p.: 74-75° C. /0.2 mbar.

¹³C NMR: 144.1 (s), 133.3 (s), 128.5 (d), 127.2 (d), 121.1 (s, CN), 37.9(t), 36.8 (d), 28.5 (t), 20.3 (t), 15.5 (q), 13.4 (q).

¹H NMR: 7.21 (AB syst. J_(AB)=8.4, 4H), 3.74 (dd, J=8.4, 6.4, 1H), 2.64(q, J=7.7, 2H), 1.95-1.76 (m, 2H), 1.58-1.42 (m, 2H), 1.23 (t, J=7.7,3H), 0.95 (t, J=7.2 Hz, 3H).

Example 2

Preparation of a Perfuming Composition

A perfuming composition for a “Savon de Marseille” was prepared byadmixing the following ingredients

Parts Ingredient by weight Verdyl acetate 100 Hexyl acetate 203-Methyl-2-hexenyl acetate¹⁾ 10 Aldehyde C 12 25 AldehydeHexylcinnamique 100 Aldehyde MNA 20 Aldehyde Supra 10 Allyl amylglycolate 20 Ethyl 2-methyl-pentanoate¹⁾ 15 CETALOX ®²⁾ 10 Citraldiethylacetal 25 Cyclopentol 30 Damascone Alpha 5 Damascenone Total¹⁾ 5Dihydro Eugenol 10 Dihydromyrcenol 200 Ethyle-2-methylbutytate 5Eucalyptus essential oil 15 Eugenol 40 GALAXOLIDE ® 50% MIP³⁾ 100Geranyl Nitrile 50 HEDIONE ®⁴⁾ 60 Ionone beta 40 IRALIA ® Total⁵⁾ 150Iso E Super ®⁶⁾ 400 LILIAL ®⁷⁾ 200 Linalol 150 10%*2,6-Dimethyl-5-heptanal 5 Methylnaphthylcetone 40 Methylparacresol 5Muscenone⁸⁾ 50 MYROXYDE ®⁹⁾ 10 10%* Neobutenone ®¹⁰⁾ 20 NIRVANOL ®¹¹⁾ 30Trans-1-(2,2,6-trimethyl-1-cyclohexyl)-3-hexanol¹⁾ 10 Paracymene 30Phenethylol 150 10%* ROMASCONE ®¹²⁾ 30 SCLAREOLATE ®¹³⁾ 100 TerpeneOrange 100 2,4-Dimethyl-3-cyclohexen-1-carboxaldehyde 10 Undecalactone50 VERDOX ®¹⁴⁾ 100 (E)-1-(2,6,6-Trimethyl-1- 60cyclohexen-1-yl)-1-penten-3-one 2615 *in dipropyleneglycol ¹⁾Origin:Firmenich SA, Geneva, Switzerland²⁾Dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan; origin:Firmenich SA, Geneva, Switzerland³⁾1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyrane;origin International Flavors &Fragrances, USA ⁴⁾Methyl dihydrojasmonate;origin: Firmenich SA, Geneva, Switzerland ⁵⁾Mixture of isomers ofmethylionones; origin: Firmenich SA, Geneva, Switzerland⁶⁾1-(Octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone; originInternational Flavors &Fragrances, USA⁷⁾3-(4-tert-Butylphenyl)-2-methylpropanal; origin: International Flavors&Fragrances, USA ⁸⁾3-Methyl-4/5-cyclopentadecen-1-one; origin: FirmenichSA, Geneva, Switzerland ⁹⁾6,7-Epoxy-3,7-dimethyl-1,3-octadiene; origin:Firmenich SA, Geneva, Switzerland¹⁰⁾1-(5,5-Dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; origin: FirmenichSA, Geneva, Switzerland¹¹⁾3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol;origin: Firmenich SA, Geneva, Switzerland ¹²⁾Methyl2,2-dimethyl-6-methylene-1-cyclohexanecarboxylate; origin: Firmenich SA,Geneva, Switzerland ¹³⁾Propyl (S)-2-(1,1-dimethylpropoxy)propanoate;origin: Firmenich SA, Geneva, Switzerland ¹⁴⁾2-tert-Butyl-1-cyclohexylacetate; origin: International Flavors &Fragrances, USA

The addition of 300 parts by weight of (2Z)-2-phenyl-2-hexenenitrile tothe above-described perfuming composition provided a new compositionwhich had a fragrance more functional, detergent-like. Moreover the newcomposition had a reinforced green-citronella connotation. Furthermore,when linen was washed with a detergent containing the new composition,the linen after drying had a powerful salicylate note, of thefloral-herbaceous type, which was totally absent from a linen washedwith a detergent containing the composition not containing theinvention's compound.

This connotation/note was lacking pineapple and rosy character.

Example 3 Preparation of a Perfuming Composition

A perfuming base for a soap was prepared by admixing the followingingredients:

Parts Ingredient by weight Verdyl acetate 200 Anisic aldehyde 270Aldehyde C 10 20 10-Undecenal 30 Aldehyde C 12 60 Aldehyde MNA 50 Methylbenzoate 60 Benzylacetone 250 CETALOX ®¹⁾ 50 Citronnelle Java 1000Dodecanenitrile 40 Coumarine 130 Cyclopidene²⁾ 60(1′R,E)-2-Ethyl-4-(2′,2′,3′-trimethyl-3′-cyclopenten- 901′-yl)-2-buten-1-ol Dihydromyrcenol 350 Diphenyloxyde 1000Ethylvanilline 30 Eucalyptol 100 Eugenol 90 GALAXOLIDE ® 50% MIP³⁾ 2503-(3-Isopropyl-1-phenyl)butanal 50 Geranyl Nitrile 90 HABANOLIDE ®⁴⁾ 300Ionone beta 180 IRALIA ® Total⁵⁾ 400 ISO E SUPER ®⁶⁾ 600 LILIAL ®⁷⁾ 650Linalol 350 LORYSIA ®⁸⁾ 300 Methylnaphthylcetone 180 Methylparacresol 90NIRVANOL ®⁹⁾ 30 Trans-1-(2,2,6-trimethyl-1-cyclohexyl)-3-hexanol²⁾ 30Phenethylol 450 Phenylhexanol 450 Verdyl propionate 200 Terpinolene 450Undecalactone gamma 150 POLYWOOD ®¹⁰⁾ 70 10%* Methyl octinecarbonate 30LIMINAL ®¹¹⁾ 100 9280 *in dipropyleneglycol¹⁾Dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan; origin:Firmenich SA, Geneva, Switzerland ²⁾Origin: Firmenich SA, Geneva,Switzerland³⁾1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyrane;origin International Flavors &Fragrances, USA ⁴⁾Pentadecenolide; origin:Firmenich SA, Geneva, Switzerland ⁵⁾Mixture of isomers of methylionones;origin: Firmenich SA, Geneva, Switzerland⁶⁾1-(Octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone; originInternational Flavors &Fragrances, USA⁷⁾3-(4-tert-Butylphenyl)-2-methylpropanal; origin: International Flavors&Fragrances, USA ⁸⁾4-(1,1-Dimethylethyl)-1-cyclohexyl acetate; origin:Firmenich SA, Geneva, Switzerland⁹⁾3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol;origin: Firmenich SA, Geneva, Switzerland¹⁰⁾Perhydro-5,5,8aa-trimethyl-2a-trans-naphthalenyle acetate; origin:Firmenich SA, Geneva, Switzerland¹¹⁾3-(4-Tert-butylphenyl)-2-methylpropanal; origin: Givaudan-Roure SA,Vernier, Switzerland

The addition of 150 parts by weight of (2Z)-2-phenyl-2-hexenenitrile tothe above-described perfuming base imparted to the fragrance of thelatter a clear floral-jasmine and salicylate connotation slightly greenand cosmetic. This connation was lacking pineapple and rosy character.

1. A perfumed article comprising: i) at least one compound of formula(I),

wherein R¹ is a C₁₋₄linear alkyl group, and a) the dotted linerepresents a double bond having a configuration E or Z or a mixturethereof, and R² is a hydrogen atom; or b) the dotted line represents asingle bond, and R² is a C₁₋₄linear alkyl group; and ii) a consumerproduct base, wherein the consumer product base is a solid or liquiddetergent, a fabric softener, a perfume, a cologne or after-shavelotion, a perfumed soap, a shower or bath salt, mousse, oil or gel, ahygiene product, a hair care product, a shampoo, a body-care product, adeodorant or antiperspirant, an air freshener, a cosmetic preparation, afabric refresher, an ironing water, a paper, a wipe or a bleach.
 2. Theperfumed article of claim 1, wherein in formula (I) R¹ represents aC₂-C₃ linear alkyl group.
 3. The perfumed article of claim 2, wherein informula (I) the dotted line represents a double bond having aconfiguration Z.
 4. The perfumed article of claim 3, wherein thecompound is (2Z)-2-phenyl-2-hexenenitrile.
 5. A perfuming compositioncomprising a compound of formula

wherein the dotted line represents a single bond and i) R¹ is a C₃₋₄linear alkyl group and R₂ is a methyl group; or ii) R¹ is a C₁₋₄ linearalkyl group and R₂ is a C₂₋₄ linear alkyl group.
 6. A perfumingcomposition according to claim 5, wherein the compound is2-(4-methylphenyl)hexanenitrile or 2-(4-ethylphenyl)pentanenitrile.
 7. Aperfuming composition according to claim 5, further comprising at leastone ingredient selected from the group consisting of a perfumery carrierand a perfumery base; and at least one perfumery adjuvant.
 8. A perfumedarticle comprising: i) the perfuming composition according to claim 5;and ii) a consumer product base.
 9. The perfumed article of claim 8,wherein the consumer product base is a solid or liquid detergent, afabric softener, a perfume, a cologne or after-shave lotion, a perfumedsoap, a shower or bath salt, mousse, oil or gel, a hygiene product, ahair care product, a shampoo, a body-care product, a deodorant orantiperspirant, an air freshener, a cosmetic preparation, a fabricrefresher, an ironing water, a paper, a wipe or a bleach.